#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:26:14 +0100 (lun 21 de mar de 2016) $
#$Revision: 178469 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/90/4029008.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4029008
loop_
_publ_author_name
'Swatschek, Jörg'
'Grothues, Lydia'
'Bauer, Jonathan O.'
'Strohmann, Carsten'
'Christmann, Mathias'
_publ_section_title
;
 A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization
 in the Transformation of Terpene Feedstock and the Synthesis of a
 C2-Symmetrical Terminal Bis-Epoxide.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              976
_journal_paper_doi               10.1021/jo402422b
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C7 H14 Cl2 O2'
_chemical_formula_sum            'C7 H14 Cl2 O2'
_chemical_formula_weight         201.08
_chemical_name_systematic        (2S,6S)-2,6-Dichloroheptane-1,7-diol
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-10-31T13:08:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                84.817(10)
_cell_angle_beta                 82.484(12)
_cell_angle_gamma                80.657(11)
_cell_formula_units_Z            1
_cell_length_a                   5.0136(8)
_cell_length_b                   5.3946(6)
_cell_length_c                   9.3077(13)
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      3.84
_cell_volume                     245.65(6)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)'
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_molecular_graphics
;
Ortep-3 (Farrugia, 1997) and Schakal 92
 (Keller 1992)
;
_computing_publication_material  'wingx (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur S Oxford Diffraction'
_diffrn_measurement_method       Omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3335
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd. Empirical absorption correction using
spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             106
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0198
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0331P)²+0.0268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.053
_refine_ls_wR_factor_ref         0.0533
_reflns_number_gt                2103
_reflns_number_total             2123
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402422b_si_001.cif
_cod_data_source_block           2538
_cod_database_code               4029008
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.8368(3) 1.2091(3) 0.98669(15) 0.0256(3) Uani 1 1 d .
H1A H 1.0077 1.2783 0.9543 0.031 Uiso 1 1 calc R
H1B H 0.6848 1.331 0.9522 0.031 Uiso 1 1 calc R
C2 C 0.8501(3) 0.9634(2) 0.91847(13) 0.0200(2) Uani 1 1 d .
H2 H 0.9901 0.8353 0.9619 0.024 Uiso 1 1 calc R
C3 C 0.9254(3) 0.9876(2) 0.75552(14) 0.0225(3) Uani 1 1 d .
H3A H 1.0887 1.0722 0.7341 0.027 Uiso 1 1 calc R
H3B H 0.7748 1.097 0.7114 0.027 Uiso 1 1 calc R
C4 C 0.9832(3) 0.7395(3) 0.68420(15) 0.0238(3) Uani 1 1 d .
H4A H 0.8214 0.6529 0.7058 0.029 Uiso 1 1 calc R
H4B H 1.1369 0.6305 0.7259 0.029 Uiso 1 1 calc R
C5 C 1.0531(3) 0.7758(2) 0.51994(14) 0.0238(3) Uani 1 1 d .
H5A H 0.8928 0.8727 0.478 0.029 Uiso 1 1 calc R
H5B H 1.2033 0.8772 0.499 0.029 Uiso 1 1 calc R
C6 C 1.1366(3) 0.5324(2) 0.44580(14) 0.0194(2) Uani 1 1 d .
H6 H 0.9936 0.4223 0.4755 0.023 Uiso 1 1 calc R
C7 C 1.1710(3) 0.5740(3) 0.28202(15) 0.0312(3) Uani 1 1 d .
H7A H 0.9968 0.6607 0.2501 0.037 Uiso 1 1 calc R
H7B H 1.3097 0.6858 0.2523 0.037 Uiso 1 1 calc R
Cl1 Cl 0.52226(5) 0.85901(5) 0.96092(4) 0.03148(10) Uani 1 1 d .
Cl2 Cl 1.45638(5) 0.37057(5) 0.50168(4) 0.03219(10) Uani 1 1 d .
H1O H 0.645(5) 1.220(4) 1.163(2) 0.033(5) Uiso 1 1 d .
H2O H 1.122(5) 0.287(4) 0.211(2) 0.044(6) Uiso 1 1 d .
O1 O 0.7989(2) 1.1830(2) 1.14099(11) 0.0305(2) Uani 1 1 d .
O2 O 1.2503(3) 0.3485(3) 0.21140(13) 0.0380(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0328(7) 0.0244(6) 0.0193(6) -0.0076(5) -0.0017(5) -0.0014(5)
C2 0.0195(6) 0.0227(6) 0.0169(6) -0.0051(5) 0.0010(5) -0.0010(5)
C3 0.0303(7) 0.0203(6) 0.0165(6) -0.0038(5) -0.0006(5) -0.0029(5)
C4 0.0309(7) 0.0236(6) 0.0158(6) -0.0055(5) 0.0023(5) -0.0030(5)
C5 0.0324(7) 0.0223(6) 0.0159(6) -0.0049(5) 0.0002(5) -0.0020(5)
C6 0.0151(5) 0.0252(6) 0.0182(6) -0.0070(5) -0.0014(4) -0.0012(4)
C7 0.0384(8) 0.0374(8) 0.0169(7) -0.0101(6) -0.0002(6) -0.0009(6)
Cl1 0.02340(19) 0.03486(19) 0.0353(2) -0.01092(14) 0.00740(13) -0.00585(14)
Cl2 0.01977(18) 0.0412(2) 0.0350(2) -0.01017(16) -0.00595(13) 0.00366(14)
O1 0.0279(6) 0.0427(6) 0.0204(5) -0.0147(4) 0.0005(4) 0.0002(5)
O2 0.0305(6) 0.0526(7) 0.0329(6) -0.0290(5) 0.0007(4) -0.0018(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C2 112.91(11)
C1 C2 C3 112.28(11)
C1 C2 Cl1 108.36(9)
C3 C2 Cl1 109.99(9)
C2 C3 C4 114.50(10)
C3 C4 C5 112.15(11)
C6 C5 C4 113.97(11)
C7 C6 C5 112.52(11)
C7 C6 Cl2 108.20(10)
C5 C6 Cl2 109.93(9)
O2 C7 C6 113.14(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4210(16)
C1 C2 1.5085(17)
C2 C3 1.5134(16)
C2 Cl1 1.8072(13)
C3 C4 1.5164(18)
C4 C5 1.5254(17)
C5 C6 1.5120(17)
C6 C7 1.5119(18)
C6 Cl2 1.8121(13)
C7 O2 1.4102(19)
